Potassium Carbonate → HCID 60043433, compound

HRID 1854608Notes

Reaction equation

HRID 1854608 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][O:23][CH3:24]>C(#N)C.O>[C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:21][CH2:22][O:23][CH3:24])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 60043433HCID 60043433, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A solution of N-Boc-piperazine (1.00 g, 5.31 mmol) in acetonitrile (30 ml) was treated with K2CO3 (2.20 g, 15.9 mmol) and (2-bromoethyl)methyl ether (812 μl, 5.84 mmol) and heated to 80° C. for 18 h. The cooled mixture was diluted with water and extracted with DCM. The combined organcs were dried over MgSO4, filtered and evaporated and the residue purified by column chromatography on SiO2, eluting with 5% EtOH in DCM to afford 1-Boc-4-(2-methoxy-ethyl)-piperazine as a clear oil (978 mg, 76%). 1H NMR (400 MHz, DMSO-d6) δ 3.41 (t, J=5.8 Hz, 2H), 3.29-3.25 (m, 4H), 3.21 (s, 3H), 2.45 (t, J=5.8 Hz, 2H), 2.33 (t, J=5.0 Hz, 4H), 1.38 (s, 9H).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organcs were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue purified by column chromatography on SiO2
  6. washeluting with 5% EtOH in DCM

Sources & evidence

ORD record
ord-52d5393012734c0d96a4bd46c37dd9ce
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

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